First, contrary to the above report, I do not smoke; it's a disgusting and vile habit.

However, back to the problem at hand: The first question has already been answered.

The second question has more interpretive possibilities. Apparently a cigar is 4/5 usable, with a 1/5 unusable stub. So, being left with 4 stubs, after having smoked 4 cigars, Cheap can make a cigar of 3/5 usable tobacco and 1/5 unusable stub. As this cigar is only 3/5 usable instead of the usual 4/5, it could in some sense be counted as 3/4 of a cigar, as we are counting the use of 4/5 of a cigar as having smoked the cigar: so he smokes 4 and 3/4 cigars, in that sense.